Nonstop flights from Cleveland to Chicago

Southwest Airlines flies this route 2 to 4 times a day.

CLECleveland Hopkins International

306 mi · 26 flights a week

MDWChicago Midway International

CLEMDW

When they leave

Cleveland time

8:50a7:20pFirst departure 8:50 AM, last 7:20 PM

One morning flight at 8:50 AM, then four in the afternoon, 12:50 PM to 4:00 PM, then three in the evening, 5:25 PM to 7:20 PM.

Every flight

Earliest first

8:50 AM→9:00 AMSouthwest AirlinesBoeing 737-700Daily
12:50 PM→1:05 PMSouthwest AirlinesBoeing 737 MAX 8Tue, Wed
1:45 PM→2:00 PMSouthwest AirlinesBoeing 737 MAX 8Sun
1:50 PM→2:05 PMSouthwest AirlinesBoeing 737 MAX 8Mon, Thu, Fri
4:00 PM→4:15 PMSouthwest AirlinesBoeing 737 MAX 8Sat, Sun
5:25 PM→5:40 PMSouthwest AirlinesBoeing 737Tue, Wed, Thu, Fri
5:25 PM→5:40 PMSouthwest AirlinesBoeing 737Mon
7:15 PM→7:30 PMSouthwest AirlinesBoeing 737 MAX 8Mon, Tue, Wed, Thu, Fri
7:20 PM→7:35 PMSouthwest AirlinesBoeing 737Sun

Schedules last checked Sep 19, 2026. Times are local.

Flying from Cleveland to Chicago

Southwest Airlines is the only airline flying nonstop from Cleveland to Chicago, 2 to 4 times a day on the Boeing 737 MAX 8, Boeing 737 and Boeing 737-700.

Flights run every day of the week, from 2 on Saturdays to 4 on Mondays, Tuesdays, Wednesdays, Thursdays, Fridays and Sundays. The first arrival in Chicago is at 9:00 AM and the last at 7:35 PM. The flight covers 306 miles.

Flying back, Chicago to Cleveland has 26 nonstop flights a week. From Cleveland, O'Hare (ORD) is the other Chicago area airport with nonstop flights, 105 a week.